editors note: this is a repost of one of my earliest letters. i do this for two reasons 1. not many read my blog in the early days (not many still do, but i have a few more readers) 2. i cant stop blowing my nose long enough to write a full post. enjoy!

Dear Shayna,

I want to thank you for making me re-think my internet dating habits: Lesson #1 – Never, ever agree to more than a lunch or a drink for the first face to face meeting, dinners are simply too long, and sometimes really painful. Like it was with you. So while you may have cost me about $40 (remember, when you offered to split it I couldn’t take you up on it quickly enough), you also taught me something priceless.

Lesson #2 – Whether it is on purpose or subconsciously, you made me realize that we all sell our selves online. We project an image of what we think people want to see in our profile, and then enhance that image through emails, online chat and dare I say – even an adult-like phone call. I think everyone does this to a certain degree; I like to think I try my best to show people that I am down to earth, witty, and pretty much the man. You seemed like a happy-go-lucky, easy to talk to, educated individual. Well, at least you are educated (I can only presume you didn’t lie about your Master’s Degree). Turns out you were actually quite miserable. Upon getting the awkward greeting out of the way, I asked how your day went. Your response, a terse, “Awful.” I’ll spare you the details, but it was only downhill from there.

Lesson # 3 – You also taught me to watch what I say. When I mentioned I was looking for jobs at prep schools, you were curious as to why only private. My answer, if you recall, was along the lines of, “Well the administrative type job I’m looking for aren’t typically at public schools, I’m not certified to teach at a public school, and I went to a private high school so I know the landscape and think I’d really enjoy that environment again.” I didn’t realize that was such a snobby comment, because you replied, “Private school kid huh? Aren’t you the privileged one.” At least that wasn’t 20 minutes into knowing each other. Oh, wait. Yes it was.

Lesson # 4 – I guess I’m not the only one who has trouble reading signals. Let’s recap real quick: You barely spoke, and when you did something miserable usually came out; you called me a snob; I scoffed at a second glass of wine and dessert; even though I have always paid on the first date unless the female absolutely insists, as soon as you brought out your plastic I think I tore it from your hands to throw in with mine; oh yeah, I shook your hand goodbye. Despite all this Shayna, you actually had the gall to send me an email the next day informing me what a blast you had and that you wanted to do it again soon. Suffice it to say, that certainly didn’t happen…and if you couldn’t read that signal, hopefully this letter spells it out a bit clearer.

See you never,

Privileged

PS – I should tell you that my guess is you were just having a bad day, and that you are probably far cooler and sweeter than you presented yourself on our date. But first impressions are everything. Sorry.

I want to thank you for making me re-think my internet dating habits: Lesson #1 – Never, ever agree to more than a lunch or a drink for the first face to face meeting, dinners are simply too long, and sometimes really painful. Like it was with you. So while you may have cost me about $40 (remember, when you offered to split it I couldn’t take you up on it quickly enough), you also taught me something priceless.

Lesson #2 – Whether it is on purpose or subconsciously, you made me realize that we all sell our selves online. We project an image of what we think people want to see in our profile, and then enhance that image through emails, online chat and dare I say – even an adult-like phone call. I think everyone does this to a certain degree; I like to think I try my best to show people that I am down to earth, witty, and pretty much the man. You seemed like a happy-go-lucky, easy to talk to, educated individual. Well, at least you are educated (I can only presume you didn’t lie about your Master’s Degree). Turns out you were actually quite miserable. Upon getting the awkward greeting out of the way, I asked how your day went. Your response, a terse, “Awful.” I’ll spare you the details, but it was only downhill from there.

Lesson # 3 – You also taught me to watch what I say. When I mentioned I was looking for jobs at prep schools, you were curious as to why only private. My answer, if you recall, was along the lines of, “Well the administrative type job I’m looking for aren’t typically at public schools, I’m not certified to teach at a public school, and I went to a private high school so I know the landscape and think I’d really enjoy that environment again.” I didn’t realize that was such a snobby comment, because you replied, “Private school kid huh? Aren’t you the privileged one.” At least that wasn’t 20 minutes into knowing each other. Oh, wait. Yes it was.

Winnie & Kevin went further at 11 than we ever will

Lesson # 4 – I guess I’m not the only one who has trouble reading signals. Let’s recap real quick: You barely spoke, and when you did something miserable usually came out; you called me a snob; I scoffed at a second glass of wine and dessert; even though I have always paid on the first date unless the female absolutely insists, as soon as you brought out your plastic I think I tore it from your hands to throw in with mine; oh yeah, I shook your hand goodbye. Despite all this Shayna, you actually had the gall to send me an email the next day informing me what a blast you had and that you wanted to do it again soon. Suffice it to say, that certainly didn’t happen…and if you couldn’t read that signal, hopefully this letter spells it out a bit clearer.

See you never,

Privileged

PS – I should tell you that my guess is you were just having a bad day, and that you are probably far cooler and sweeter than you presented yourself on our date. But first impressions are everything. Sorry.